The Tomboy in the Suit

I am writing to you in hopes for some advice on how to change from a “tom boy look” to a mid-level executive in a financial institution.

I know that your blog is mostly geared toward New York lawyers, but while I am neither of those (Dallas, Tx – Financial Analyst), I am confident that you can help. A little bit of background…I grew up in a very small town climbing trees and playing with boys. In college, my dress attire was jeans and over-sized T-shirts. It wasn’t until my senior year that I started wearing T-shirts that fit.

Making the transition from college life to financial institution was a little easy back home, (South Texas/Rio Grande Valley), but now that I reside in Dallas, I feel that my current wardrobe isn’t cutting it. My current attire is grey slacks and a button down or simple one-tone blouse. While I mentioned my basic attire, please note that I own about 2 pairs of slacks/dress pants (black and grey) and 2 button downs (purple and maroon).

I have a pair of black shoes and I wear those with black dress socks.

I have never been a “girly-girl” (not that I am opposed to it), but I have always lacked the ability to match colors and styles without looking hideous.

This is a great question, A. What you’re wearing doesn’t sound so bad to me (albeit a bit boring, but there’s nothing unprofessional about that), but the vibe I’m getting from your email is that you don’t feel elegant, feminine, or sophisticated. I think it’s important to distinguish unprofessional attire from attire that isn’t elegant/feminine/sophisticated — there have been a lot of very, very successful women who wore nothing but boxy suits, had masculine haircuts, and wore clunky heels (or flats). In fact, to a lot of older people (both men and women) that is the best way to convey that you’re serious about your job. (I was just reading a comment on an older post about whether long hair is appropriate — the reader noted that when she ran for office, no one took her seriously until she cut her mid-back-length hair into a Hilary Clinton cut.) (Pictured: Tomboy Shorts, originally uploaded to Flickr by FredoAlvarez.)

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That said — my own attitude (and the ethos behind this blog) has been that today it is possible to walk the line between something feminine and fun, but still be professional. Sometimes we have debates on what’s appropriate for the office (see today’s TPS); sometimes it really just depends on what’s right for your office. There are some easy ways to add feminine flair to your outfits, though, that should be pretty safe advice no matter what your office.

1) Add heels. They don’t have to be high; in fact I would recommend starting with what you can walk in. (You may want to check out our Guide to Comfortable Heels, and the comments there!) Keep in mind that as you get better in walking in heels, a slightly pointy toe and a skinny heel will be the best way to elongate your legs and make your look more feminine. How pointy a toe is appropriate is something that changes with fashion — long pointy toes were popular a few years ago (looking back, some almost looked like elf/witch shoes!); nowadays a very slight point is popular. I would suggest looking online at some of the high-end brands, such as Manolo Blahnik, Christian Louboutin, and Ferragamo, to get an idea of what your ideal shoe right now would be, and then looking in whatever range your budget/walking ability allows.

2) Add jewelry. I’m a big believer in jewelry adding a lot of personality to your outfit. To start small, you may want to get a good set of fake pearls to try out how those feel with your button-downs and t-shirts. (You can always invest in a better set from Mikimoto or even your local jewelry store later on.) Similarly: what watch are you wearing? If you’re wearing a sporty watch, this might be a good time to investigate how a more feminine watch might feel, either with a leather strap or a metal strap. Earrings are the third “start small” piece that I’d recommend. Personally, I hate posts, but I feel like dangly earrings are inappropriate for many offices (and distracting if you move your head a lot) so to me the perfect office earring is the “huggie,” so named because they’re hoops so small that they hug your ears.

3) If you’re not already wearing makeup, add some. It doesn’t have to be a lot — sometimes just a lipgloss with a slight tint is enough for women. (It’s a bit too light for me, but a number of friends love Fresh Sugar Plum Lip Treatment SPF 15, or I’ve written before of my love for CoverGirl Lipslicks. Clinique Almost Lipstick is another classic.) Have a good friend help you with this if you’re really clueless — how does your face look right now? For me, I know I look a lot prettier when I add concealer under my eyes, curl my eyelashes, and add a bit of blush and a bit of color to my lips — I generally don’t leave the house without those. For work I also wear mascara, eyebrow pencil, eyeliner, lip liner, and lipstick; for nights out I’ll wear 3-5 different shades of eye shadow as well as a few more coats of mascara; I’ll also use a highlighter like Touche Eclat or wear a sparklier blush, like NARS The Multiple Orgasm. My point here is that makeup is not an all or nothing proposition — it’s a continuum, and even just wearing a little bit can help you look and feel more feminine.

4) Find inspiration in a celebrity or public figure (anyone who’s photographed often), or even a character on television. I would recommend looking for someone with your body type to get the most out of this exercise. Take note of what she wears — how does the fit of her clothes differ from yours? Is there a color combo that she wears that you could try? How about her jewelry and shoes — can you add more personality to your outfit that way? Another option here would be to find a few static photos of this celebrity/character that you really love — I would say 6-10 photos — and visit a personal shopper (such as one at your local department store), or even a personal stylist. For my $.02, I think it’s important that you go in with an idea of what you want to achieve before you meet with them, but maybe that’s just me.

Readers, what are your best tips to add femininity to the professional wardrobe? What do you think about Reader A’s question?

That being said, I still don’t wear any make up or heels. I buy nice flats, make sure my hair is groomed and I wear mostly cabochon stone jewelry (think onyx, turquoise, etc. not diamonds, etc.). The wardrobe of the female senior partner at the firm has been something I try to emulate while making sure I feel physically comfortable in what I’m wearing.

I rarely wear make up and my jewelry in minimal, but I wear well-fitting clothing with nice fabrics and keep my hair groomed. It’s a common look among the senior women in my company, and I have no urge to change.

I bet many of us have been in your shoes. I didn’t know how to dress professionally when I arrived at medical school, and I was broke broke broke. Over the last ten years, I’ve upgraded my wardrobe considerably and been able to take more chances with adding feminitity. A few additional ideas:

1) Depending on your price range, a personal shopper at a high end department store could be awesome. They will push you to try on all sorts of things. Some you will hate, others will be surprisingly pleasing. Don’t let them talk you into something that isn’t you, but do give yourself the chance to experiment. For instance, an embellished shirt (sweater with ruffles, I’m thinking) may “feel” like you but have a little more feminine punch. They also may push you to try colors you don’t tend to gravitate to, but may be surprisingly flattering. I find that print silk blouses are very comfortable, but made me feel pretty and girly

2) Do you have a close friend whose dress you admire? If you are comfortable, ask them to go shopping with you. She may be able to encourage you to try new things.

3) If you are comfortable, if there is someone at work who’s personal style you admire (and you think, hey, if I knew how to do it, I wouldn’t mind dressing like that) ask her where she shops. It might give you some ideas.

4) it’s okay to not transform overnight into super girly girl. I rarely wear skirts. In my profession, pants are much more practical, and I’m more comfortable in them. So it’s okay if you come to similar conclusions about certain items. Not every style or garment works for everyone.

5) This is the hardest, but for me, it took a lot of positive self talk to get me to a place where I felt okay about spending money on myself. I have and had a lot of negative self talk about my body, and my internal commentary was preventing me from selecting clothes that were flattering or becoming. There was this constant hum in the background essentially telling me that I wasn’t pretty enough to wear nice things. My husband was actually the one who sort of broke that record for me, and while I still have bad days and bad shopping trips, I’m much more likely to try something on as an experiment, rather than assuming “I’ll look terrible in that.” That may not be your issue, but those kind of feelings definitely drove me to more boring/bland clothes.

@EC MD Wow some great advice there and #5 resonates so well with me. I too have been trying to up my working wardrobe and it has been hard to spend money on myself both because of body image and budget. My two girls have been my biggest supporters and often remind me that a) I deserve to look good and feel good about how I look and b) that they deserve to have me looking good and not like another frumpy mom.
Thanks girls and thanks to Corperette for being there too!

I am also in Dallas. I recommend using the personal shoppers and Nordstrom to get you started. They work for free. Give them your measurements (or go in and have them taken) and tell them basically the look you are going for and the amount you can spend. They will pull a varient of items for you to try on. Once you have a few basic pieces that have been brought to your attention by a pro, you’ll have a better idea of what to look for when you shop by yourself.

If I knew more about where in Dallas you live/work/shop and what your budget is, I’d be happy to recommend more.

This was exactly what I would recommend! I think Dallas, in particular, seems like a very image conscious place, and if you’re not sure how to put things together yourself, it makes a lot of sense to get help from someone who does, and who knows the area’s culture. Good luck!

I second this. I’m in Houston and work for a large bank and I went to Nordstrom to get some help pulling together my look. I had two problems–first, I had a closet full of clothes but nothing to wear. The second problem is that I spend a lot of time speaking in front of a group of people who outrank me in title and salary, so I need to look more like them. I now have 1/3rd the clothes, but everything works together (and I’m actually spending less money) and I have the look I want and need.

When I got started, I pulled pictures of celebs whose look I liked out of magazines. The first two visits, I tried on everything that she pulled and took photos–making no judgements right then. I then had my mom and best friend go over the photos with me for a week or so and then I went back and bought several of the items. It took looking at the pics of the “revised” me a few times and getting some feedback before I was totally comfortable. This way, I had time for the shock of the new look to wear off. The one thing I liked is that my shopper actually helped me work in pieces from other stores. For example, I really like the Brooks Brothers no-iron button downs and I have bought a dress or two from Talbots. I just bring in pics and we make it all work together.

I sympathize with Reader A–that’s been me. I don’t think you have to go as feminine as this post suggests, though. I’m still working on figuring out a style that is comfortable for me on all levels. I know that when I do figure it out, it won’t be super-feminine–that’s not who I am. I do want to look put-together, but believe it should be possible without needing to go very girly. Good luck, Reader A!

I am not sure the OP was actually asking for advice on becoming more feminine. That appears no where in her post, unless maybe I missed something?

The OP asks about how to transition to a mid level executive — to me that reads as advice re: how to be more polished, not how to be more feminine.

I bring this up because I think if you’re not instinctively drawn to pearls and heels and “feminine” colors, you’re not necessarily going to feel (or look) comfortable in them. And, frankly, you don’t need them to look polished and, in fact, it may hurt, not help. I work with 2 women who are rather “tom boyish” — one always looks very put together and projects a great image of authority. She has a short, no fuss haircut, wears lots of cute loafers and oxfords, a chunky watch, minimal jewelry and really great cut suits and button down shirts in neutral colors. It really works for her! The other woman does the whole pearls, small girly watch, the occasional bright color sweater or print blouse, but she looks incredibly uncomfortable and not like herself, if that makes any sense.

I do think the really good advice is to find someone — on tv or in your real life, wherever — whose style you like and feel comfortable with and take it from there. I think we are lucky to have some room to negotiate what is “professional” as women, and it’s important to find a look that works for you, individually, so you don’t feel like you’re playing dress up, but feel like your work wardrobe reflects who you are as a professional.

Yes, well said, AIMS. I read this comment and then went back over the post, and I agree.

I’m reminded of some “What Not To Wear” episodes in which women were pushed into a feminine look that just wasn’t them. It’s as if it goes without saying: feminine is mandatory. I’m one of the girliest girls I know, and would hate to go without heels, makeup, etc. But I feel very strongly that other women should not feel they have to dress that way in order to to look professional, confident, and what have you. There are other ways to do it–find YOUR style!

As I read Kat’s response, I thought this exact thing – Reader A never asked for advice on dressing more femininely, she asked for advice on how to dress more professionally. The two don’t necessarily have to go together. Well said, AIMS.

I think the advice to add heels is the poorest part of the post. Someone who is tomboyish may have a hard time walking in heels, and feel awkward and uncomfortable. Anyway, the whole have-to-wear-heels is such a dated ’80’s look anyway … Here in the year 2011, women in the professional world wear great shoes at all heel levels.

It’s a lot easier for a tomboy to adjust to some light, well-done makeup and jewelry than to heels, IMO.

But I do have to ask, when I see these kinds of things (and I’ve known women IRL with these issues too). Where were their parents? Did their parents completely absolve themselves of teaching their daughters how to dress for situations that called for other than jeans and t-shirts? It’s shameful, IMO. Part of being a parent is teaching your child how to dress for situations and that includes how to rock a polished, professional look when the situation warrants.

I re-read the post and decided to comment as a result of this line of comments and because of your comment that “The two don’t necessarily have to go together”. I agree that feminine doesn’t necessarily equal professional. But the sad reality is that the correlation shouldn’t be thrown out the window. Most people, especially women are judged (at least partly and initially) due to their appearance. I do not think Kat was recommending a total Fem. makeover. She gave options that could be easily tailored to Reader A’s sensibilities. It is just so happens that “feminine” is commonly considered “put together”. Also, it seems to me that better fabrics and cuts tend to be more flattering and this can be interpreted as looking more feminine as well.

I agree with Barrister in the Bayou. In the corporate world for women, sometimes little things that would be considered “feminine” are key to a woman looking polished. For instance, unless you are one of those rare (and lucky!) women, most women need at least some makeup to look put together or at least not tired. I’m definitely not a girly-girl and I don’t wear a lot of makeup, but I always put on a little concealer (especially under my eyes), a blush or bronzer, and some mascara so I look healthy and put together and not tired. Also, a suit jacket, blazer, or even a sweater with a belt helps finish an outfit and create a more polished look. If you don’t want to wear a jacket or outer layer, some accessories like a statement necklace, belt and/or earrings can help make an outfit look more finished. Don’t think “girly” so much as “finished”. You can be flexible with the type of necklaces — they need not be pearls; look for a nice combination of neutral metals or look for accessories in earth tones. Even male executives wear accessories — watches, cufflinks, lapel pins. Accessories help finish an outfit the way icing finishes a cake. And while we’re eon the subject of gender, I’d like to address the whole gender/feminine issue that’s come up. This is not a double-standard issue for women. I have spoken to my male colleagues about this after hours. Don’t think for a moment that male executives don’t do the exact same thing with their wardrobe or size-up their counterparts’ attires. In some ways, they can be worse than women. Some male executives obsess over things like suit brands, material quality, accessories (such as watches, cufflinks, monogramming, etc.) more than women. Worrying about looking polished and “dressing the part” in management transcends gender.

Another really simple thing is just the addition of color. I’m not necessarily saying everything you own needs to be like bubble gum pink, but maroon, black and grey (and some shades of purple) just seem more masculine — I think it’s a certain starkness. Pastels obviously feel more feminine, but I think just the insertion of other, paler colors will help. Especially in the South, and I think that goes doubly for Dallas.

Wear a dress! Dresses are easy because you don’t have to match (except for maybe a cardigan to wear over a sleeveless dress) and they are instantly feminine. When I first started working many girls I worked with thought I dressed really well. In reality, I just wore dresses every day and the fact that I wasn’t wearing pants and a button-down amazed them.

I agree completely! This has been my secret for 25 years. Dresses are a double win if you’re on the short side, since they can make you look taller as long as you don’t buy ones with a silly contrasting color blocks along the hem or at the waist. Also, dresses in permanent press fabric can look very expensive and nice looking, if you shop well. The same isn’t necessarily true of blouses, and suits almost always have to be dry cleaned.

Not every year is a good year for buying dresses for work. A few years ago was great. I bought like 10-15 dresses, including five from Target. That way I was in good shape for a few years, in case there were fewer flattering dresses out there.

it’s true re: cyclical nature of good dresses. sometimes there are no dresses I want to buy, sometimes there are 10. Since January I’ve bought three, which I think is a pretty good haul (esp because all of them have sleeves and two of them have a matching jacket)

I really like the Calvin Klein dresses and skirts (I get mine from Macy’s) – fwiw I’m plus size and have been very happy with the cut, quality, etc. of the CK dresses (and slacks and other CK plus size items). I felt a little silly wearing dresses to work at first, but a good friend pointed out that she views it as getting to wear something “as comfortable as pjs” to work while still looking professional. My advice with the dresses is to stick to getting them plus a jacket or two from the same line, that way the fabrics/colors will match up and you’ll have more options.

I’ve been trying for several years to break out of my “comfort zone” of black pants/neutral sweater or T-shirt. If you have time to spend or live near a shopping area, challenge yourself to shop once a week or so and try on at least three things that are different. Make a point to buy one new piece every week or two. Then slowly incorporate the new pieces into your weekly rotation. I’ve never liked making drastic changes, because then people comment about it making me uncomfortable.

I have also had luck asking a Banana Republic employee to help me out on a very slow morning or afternoon. Some of them will try to upsell you, but some are far better at matching clothes than I could ever dream to be.

A – I completely understand what you mean. I have such a hard time putting outfits together that are feminine and match. My solution is to wear a ton of dresses. Dresses are so easy to throw on and they look very put-together and feminine. Even something as simple as this sheath dress -http://bit.ly/lo43Xs – with a black, white, or colored cardigan and simple pumps or pointy flats will look great for work. Or, if you wanted to do something more feminine, a shirtdress like this one – http://bit.ly/iOzc9M- is very girly while staying professional and looks like a cohesive outfit.

Also, I second the suggestion to use a personal shopping service. I love the personal shoppers at JCrew, they’re good about bringing you lots of options and usually don’t pressure you!

As a colloraly to this: avoid skirts, until/unless you really know what you’re doing or want to spend a lot of time on clothes. I didn’t realize this when I first started playing with clothes, but skirts are pretty hard to match with appropriate tops (unless they’re really simple pencil skirts). Both dresses and pants are much easier to create outfits with.

Looks like my voice is the lone dissent so far, but I don’t think a woman’s appearance must be traditionally and stereotypically feminine to be professional.

I’m not entirely sure what the OP is asking here, because I think she can be every bit a woman AND a professional in flats, trousers, button-down shirts, a Glenn Gould wardrobe palette, and no makeup. If it’s reassurance she wants, she gets it from me.

Word. It doesn’t seem like the original poster is really looking for help being “girlier” but rather more pulled together.

I would recommend looking for better constructed versions of the types of clothing that you gravitate to in slightly better materials.

Also, one big thing that I had to get past on my own journey to more professional dressing was that it was “ok” to care about how i looked. For a long-time it felt overly shallow to care about how I dressed and that somehow I was not pretty enough to care about looking nice. But then I realized two things: 1) your appearance for better or worse impacts how people perceive your work and 2) looking nice actually takes work. Few people actually look great if they don’t put in a little elbow grease and if I put in that bit of elbow grease I can really look nice too.

This. Second better fabrications, but also tailoring, so you don’t look sloppy. And rather than going for heels, you can also just go for better quality shoes in general (loafers, oxfords and other flats).

I agree. I wear make-up, for example, but I don’t like the suggestion that it’s necessary. And I hate, hate, hate the idea that you must wear heels to be professional: they’re bad for your feet, and bad for your back. I love pretty shoes, but there are plenty of pretty, polished non-heeled shoes out there. That something that is, literally, bad for your health is deemed a professional necessity infuriates me.

I would second this, one does NOT have to be feminine to be professional. If OP has always felt very tomboyish, then she should stick with that, but just look for ways to ‘grow up’ her wardrobe and look more professional.

On another blog some women were asking for help dressing more professionally in pants rather than skirts, and someone made the great suggestion of looking for celebrities whose style you like. People suggested Ellen DeGeneres as someone who always looks very put together and chic, but in menswear. I mean, look at Katharine Hepburn! She looked amazing and fabulous, and insisted on wearing pants. And even looking at well-dressed young guys for inspiration: Ryan Gosling for example. The Sartorialist http://thesartorialist.blogspot.com/ takes lots of street fashion photos, and lots of the guys have some amazing menswear outfits that I think would look great on more tomboyish women. I think the answer is buying good menswear-style pieces, getting them tailored well, and using the right accessories to pull things together: watch, shoes, belt, even cufflinks and pocket square.

“I think it’s important to distinguish unprofessional attire from attire that isn’t elegant/feminine/sophisticated — there have been a lot of very, very successful women who wore nothing but boxy suits, had masculine haircuts, and wore clunky heels (or flats).”

Very good point. The Dress For Success gospel can be preached too much.

I agree with suggestion to consider hiring a personal shopper or stylist. Get someone who will analyze your tastes, shape, work environment and suggest clothes that will work for you. Before doing that, get a free subscription to a program like www.Evernote.com. Create some “notebooks” named things like “Potential Office Shirts, etc.,” “Potential Office Trousers,” “Potential Office Jackets,” “Potential Office Suits,” “Potential Office Shoes.”

While browsing the web, any time you see an article of clothing that you like (shape, color, pattern, whatever), clip it to the appropriate Evernote notebook. You can also scan in images and make notes in other ways.

You might get some ideas by signing up for a free account with www.boutiques.com. Clip images of anything you like.

After you have a good selection of items, make an appointment. Bring your laptop or print out the images that most speak to you. In this context, it’s much better to be able to show someone something concrete rather than relying on a description.

Here’s another idea: sign up for catalogs from a bunch of retailers. Go through them and rip out all the pictures of outfits you like. Then try to recreate them with items in your wardrobe, and buy the missing pieces.

Pay special attention to what jewelry, shoes and handbag were paired with the outfit. Over time you start having a more intuitive understanding of what goes with what.

Regarding lip tint, I recently discovered Kuumba Made Lip Shimmers. I bought a tube in Sedona and it feels just like lip balm but adds a pop of color. I also like the lip tints and glosses from Kiss My Face. Both brands are vegan & not tested on animals.

Threadjack!! Kate Spade is having a sample sale today and I’m looking for a new bag — something large enough to carry a FEW work files plus regular wallet, cellphone, keys etc. Needs to be a neutral (which can include metallics). I would love your advice, ladies — link is here: http://www.katespade.com/handbags/sample-sale-handbags,default,sc.html

Go with the griffen! I have last year’s version and it is awesome, you can fit a ton more stuff than it looks like it can and it is great for putting a punch of color into your outfit if you go with the red

I completely agree sympathize with you, A. One of the things I’ve tried to focus on this year is both finding out what works for me as a personal style, and being okay with who I am.

The first was to get a strand of pearls – I think I spent about $50 for freshwater pearls of a decent size/quality from Overstock.com. Not that much more expensive than decent looking fakes – and they feel so much nicer.

The second was to get some clothes that fit well. Taking pants and shirts to a tailor made a huge difference.

The third was to be okay with who I am. While I find high-heeled pumps to be very elegant for work, they do not work at all when I’m in London for work. Nothing is more embarrassing than getting repeatedly getting your heels stuck in the sidewalk in front of senior management, leaving you hobbling shoeless in the rain. Switching to black dress loafers to wear with my (pants) suits made a huge difference. Plus, I never walked that elegantly in heels anyways – and since I’m no longer paranoid about tripping/falling, I can actually focus on the things that matter.

I 100% agree about the clothes that fit well. Whenever I wear a too loose sweater or pants that are too lowrise to sit right on me to work, I feel uncomfortable and unprofessional. I have been making a pile of things to donate so that I stop wearing this stuff.

I’m not big into makeup, but I recently switched from my regular moisturizer to a tinted moisturizer, and I think it evens out my skin tone, which makes me feel more confident.

I’m also in Dallas, and I’ve had the same issues about form vs. function! Give me dance pants and a t-shirt any day :) However, I’ve found a few things to help me enjoy my professional and more feminine appearance:

I recommend a color wheel to help with the matching issues. Color wheels are based on the science of what looks good together and why, so it takes the guess-work out of pulling colors and deciding if they look right together. I would also recommend taking a walk through some of the ultra-young and ultra-“girly” stores to see how they pair different colors and textures, just to get some ideas that will pull you out of your box. I’m bad about wearing the same color/cut/texture all the time, but noticing when a combo looks good on someone else or a mannequin has helped me take a few baby steps outside my comfort zone.

I’ll second the wear a dress/skirt and heels suggestions. I’m most comfortable in black on bottom and solid button-down on top, and I’ve found that just switching from pants to a skirt really helped me feel like I kicked it up a notch. Also, adding heels boosts my confidence, since it makes my walk much more authoritative. I’m also a one pair of black and one pair of brown kind of girl, but I bought some heels with a little texture to give them some personality. Instead of a matte black finish, maybe try a subtle tweed or croc print that’s the same color of the shoe, but adds just a touch of pizzaz.

The layout of the color wheel is scientific as it is based on the physics of light and the artifacts of the human visual system. There’s nothing really scientific about using the color wheel to pick colors that look good together. It’s very easy to use a color wheel to come up with color schemes that are either hideous (for example red and green, or yellow green and orange) or unsuitable for a given purpose. Getting useful results out of a color wheel is still a matter of skill and aesthetic preference. Play around with http://colorschemedesigner (dot) com for a while and you’ll see what I mean.

While I agree that you can come up with some combinations that are hideous, I’ve found the color wheel to be a useful first step in getting out of my box. I tend to think that “only” black or grey matches everything, which is not the case. For example, I would normally only pair silver jewelry with a blue shirt, but certain shades of yellow, green, or coral might go really well. This combo would never occur to me if I didn’t either see it on the wheel or see it on a mannequin.

Also, love that link, that’s actually a cool tool… in spite of some of the less-than-pretty combinations it spits out!

Start off with just tweaking your current look. There is no reason to automatically jump into dresses and you’d probably feel uncomfortable doing that. Your style can be professional without being “girly-girl.” If you like slacks and button downs, start with slacks and button downs. Evaluate whether your 2 pairs of pants are looking haggard. Even if you have a limited wardrobe, make sure that the items fit you well. Nothing has to be tight but look for gaping in the waist, wrong hem lengths etc. The same is true with button down shirts. Try out different cuts at different stores and test out what feels the most crisp and comfortable. I seem to remember there being a Brooks Brothers outlet store near Dallas. Once you have the basics down, you can work on jazzing things up a bit. Maybe try grey or aubergine shoes and a fun necklace, belt or watch. Working with those slacks, try a jacket and tee instead of the button down. As it gets hotter, you can swap out the slacks for a basic grey or black pencil skirt. Most importantly, even if you look at others for fashion inspiration, don’t try to mimic somebody else and lose your own style.

Just reread the OP and it sounds like (1) she doesn’t have many clothes at all, and (2) she doesn’t know how to put together outfits that look professional. I think that the personal shoppers people mentioned above would really be able to help with that. Good luck! :)

I’ve been this person. The easiest and least expensive way to go a little girly is via patterned blouses, or tees with a slightly ornamented neck. The best executive route, i.e. more expensive, is by upping the fabric and cut quality of your suits/blazers/ pants, to add some drape and flow. We Sturdy Gals have to take it one little step at a time:).

Reader A/OP: go look at Lisa’s blog: www.amidprivilege.com — When I was reading your email, I thought immediately of her blog and especially her business looks. Go look at her posts about “Sturdy Gals” — and Lisa? Can you post the link to the article you wrote recently about figuring out your business wardrobe based on the kinds of interactions you have? I’ve looked and I can’t remember where it is.

You guys are making my hitherto quite uneventful day into one to remember:). Here’s the link. I took software development methodology, in which one builds “Use Cases,” and described a way to get your work wardrobe set up. http://bit.ly/mzyygV.

I read this post (and comments) with interest because I always felt I was a tomboy. I never feel elegant. I have been having a fashion crisis over the past year and have finally found what I think is MY STYLE. But it took a lot of energy to figure it out. I never knew if I wore what I wore because it was available in my size (at the time, very plus sized) or if I wore it because I actually liked it. Now that I’m smaller, I have unlimited options and it’s overwhelming. Who am I? What is my style?

I started with color and decided my core colors would be black and gray. I also liked india teal and plum. I look great in cobalt blue (blond & blue eyed) so I added that too. That’s it. I wear those colors almost exclusively with black being the predominant color.

I never wore skirts or dresses because I was obese. I just couldn’t do it. I now have a couple skirts and a dress. I like them but I’m still nervous wearing them. Instead, I found that really nice dress pants that fit well look as nice if not nicer than a dress.

I also learned to trust others and their view of what I looked like because my own view is skewed. I still pick up size 12 & 14’s and think that is my size but the reality is that I’m in the 4-6 range. I can’t SEE what I really look like.

A store that has helped me tremendously is White House|Black Market. Their staff is incredible. If I go in the store, I typically spend 2-4 hours there at a time. Literally trying on everything they shove in my room in whatever combinations they tell me.

I’m not a lawyer so I don’t have to dress formal but I like to look nice. I like to look better than the average person around me. Right now in my new job that means nice dress slacks, heeled shoes, cami & sweater or jacket. It’s not fancy and it’s not overtly feminine either but I feel comfortable in it and I look good. I’m branching out with make-up and wearing lip gloss and mascara. A nice ring, bracelet or necklace to top it off and I’m good.

Literally the thing that has helped my self-image the most is my hair. Find a good stylist and colorist (if you want), spend the bucks and trust them. It’s worth it. If my hair looks good then I look good even when I’m dressed casually.

I’m never going to be a girly-girl and I’m good with that. But I don’t have to be a tomboy either. There is a happy medium for me. :)

I think the hair thing does make quite a difference. The boss character on the show The Mentalist (‘Agent Lisbon’)…technically, what she wears is really tomboy-ish and always dark colors, mostly black. But she looks great! I think it’s just the combo of good hair, good quality suits and good tailoring. That combo is all you need to make tomboy look awesome.

As others have said, you don’t need to change your personal style in order to look professional. Instead, focus on acquiring high-quality, polished ensembles that will make you project an image of competence and professionalism.

I assume a finance exec can afford to spend a reasonable amount of money on wardrobe. I would consult with a personal shopper and spend the money to buy five or six high quality go-to outfits as a start. Well-made pieces will look more polished and professional, and a personal shopper can help you put together entire outfits, so you don’t have to worry about what goes with what. Get things tailored as needed for a good fit. I’d suggest trying high-end department stores like Nordstrom, and classic professional attire stores like Brooks Brothers.

Eventually, you should build up enough of a professional wardrobe that you can go about 2 weeks without wearing the same outfit twice.

If you’re not an earrings and makeup type, then don’t wear them. But if you are interested, simple pearls and a classic watch add elegance and polish to an outfit. Your personal shopper can help you find those too. Adding lipgloss, mascara, and a bit of concealer may help you feel more feminine, if that interests you.

The easiest advice I have is to look for tailored pieces of clothing that don’t just hang straight on your body, wear subtle patterned shirts with dark bottoms, and wear a feminine shoe. Also, a great haircut and some diamond studs in your ear add polish without too much trouble. A tiny bit of makeup that takes 5 minutes or less to apply and you look very professional but not high maintenance.

I am a plus sized person, so I don’t know all the shops to reccomend, but there are many chain stores that carry easy to match separates– Ann Taylor or Jones New York for example. It’s easiest to use this type of store because they have things that go together but not so much that you get overwhelmed. I’d take a saturday, go to a mall, and try on as much as you can. Try on things you would never, ever have thought about buying. You will be very surprised what looks good on you.

Your wardrobe has some good staples in it. I don’t think I could function with only two pairs of pants, though. You need variety or people will start to notice your lack of wardrobe. I would start out with a few new pairs of pants– black fades over time and you want it to look sharp. Look for pants that have a good cut for your body (I know, that’s so general, but everyone looks good in different cuts). For me, bootcut pants work best. Target has some Mossimo black pants that I love. They are lined and have great shape to them, for around $24.

Feminine shoes are really easy to find and are an easy way to add color if you want to. I like pointed toes, but ballet flats and rounded toe flats look good also. Scarpasa.com is my current favorite for low heels and flats. If I were you, though, I’d go to a shoe store to try things on. Sofft brand shoes are super-comfortable and feminine.

A suit jacket with some tailoring can look very professional but not stuffy. Also look for patterned shirts that will obviously go with black or grey but with some color to them as well.

A good haircut does wonders. A woman I work with has a really simple, short haircut that looks amazing because of the subtle layering and the highlights. Ask someone with great hair who they go to, and go there. Tell the hairstylist what you are looking for and let them do their thing.

And finally, a structured handbag always looks good. I find bags at Ross. If you want to splurge, there are a lot of nice bags out there.

I wanted to add that I practice law in a small west coast community, and have always found this blog to be very helpful. It isn’t just for New York attorneys, that’s for sure. Commenters come from everywhere, and it is (usually) a very friendly, helpful place. Just watch out for trolls :)

I don’t understand why some people seem to resist wearing make up. I would never consider going to work without a bit of concealer under my eyes and a touch of blush on my cheeks. To me it’s less about looking “feminine” and more about looking in control and competent. A touch of make-up can be applied in under a minute that makes you look more awake and healthy. I’ve had people comment that I look wide-awake and cheerful after being at the office for an all-nighter- and have heard other associates who look frazzled and exhausted almost bragging about the fact that “they’re too busy to bother with make-up.” Go to a make up counter in a department store (I recommend Nars or Laura Mercier) and tell the salesperson that you want a routine that takes 2 minutes that will brighten your look and make you look well-rested. This is by FAR the easiest/least expensive way of make yourself look more polished and capable.

I disagree. I have met plenty of women who don’t wear makeup and look very professional and put together. My sister typically has more of a tomboy look and wears pants and flats to work. The biggest change for her to look more polished was to get a drastic haircut. She had long hair (below her shoulders) that tended to look stringy/weighed down and made her look about 5-10 years younger than she really was. When she got a shorter bob, she looked a lot more polished without really haven’t to do much else to change her look. Her hair is now a lot easier to maintain. She has fairly good skin and really doesn’t need makeup to look polished.

The easiest/cheapest fix is really going to vary by woman. Some women have great skin but could use a hair fix or more tailored clothes, while some may need help with their skin but already have amazing hair.

Make-up isn’t just about looking professional it’s also about feeling better about ourselves. Many women feel better about their looks when they wear even colored lip gloss. The better we feel about ourselves the more confident we are on the whole. Make-up isn’t a necessity by any means but anything that helps a woman feel beautiful and confident is a worthy thing.

To underscore a point made by others: tomboyish does not mean unprofessional. You don’t have to remake yourself from a pants-and-plain button-down type into a character from Mad Men to look the part in management.

It’s perfectly possible to look professional in pants if skirts and dresses aren’t your look. Look at Hillary Clinton and Angela Merkel for example. Their styles aren’t especially feminine but that hasn’t held them back in any way.

I’m short (5’3) and chubby (14) and wear dresses and skirts all the time. They define my waist much more than slacks do, especially with a tucked-in shirt or belt. Definitely try a personal shopper – s/he’ll be able to pick things that work for your figure and put together outfits you might not of thought of!

Wrap dresses, mock wrap dresses, and high-waist dresses look fabulous on curvy girls. Buy some cheap camisoles to wear under them (I cut mine off just below the chest) or, if you can find one in your size, wear one of the new cami-bras. (Nordstrom has a great one.) It’s true what they say on What Not to Wear: if you find dresses that are fairly fitted just beneath your bust, where your torso is the thinnest, you will look and feel thinner. Incidentally, if you don’t already shop in the petite department, and if you might be able to fit into, say, a size 14 or smaller, look at dresses there. It makes a huge difference. And forget about Diane von Furstenburg wrap dresses. Unless you’re fairly tall, they are too long waisted.

I want to repeat the advice to upgrade the styles with which you are currently comfortable. Get nice slacks, nice flats, and some silk blouses. I like the advice to look for tops with slight feminine details, which can make them look more finished than a t-shirt, but just as easy and comfortable to wear. The advice to work with a basic color palette makes dressing easier, too.

Also, get great undergarments!!! The tomboys I know never got a well-fitting bra or real pantyhose. It makes a huge difference. Go to Nordstroms, or another high end department store (not Victoria’s Secret) and get fitted.

I think it depends. If men are wearing suits, women should be wearing jackets too. It looks so unprofessional when you go to a meeting and all the men are in suits and there are women wearing sleeveless dresses or slouchy cardigans. But in a business casual environment, then no, a jacket’s not necessary.

Depends on your profession. If you’re in a jacket-wearing profession, then you need a jacket. Otherwise, you don’t.
That being said, I think a jacket always looks more polished than a cardigan. Sadly, for my line of work, a jacket would be way too much.

Does anyone know if there is a website that publishes the wardrobe details of film and TV characters? I’m thinking of the wardrobes of Vera Farmiga in “Up In The Air” and Julianna Margulies in “The Good Wife.”

Aside from adding some light make up and some cute jewelry, I think she should make sure to pick up some tops/blouses in some lighter, more girly colors. Pale pinks are usually easy. If she gets a friend whose opinion she trusts, even a floral or small cutely patterened blouse could go a long way.

better fit (tailoring, better fabrics (higher end) and drape, and accessories. silk scarves can add an element of polish and style to otherwise very dull outfits, very executive looking in my view.
…and never being inappropriate- ie too much skin or too tight.

You have 2 button down shirts now right? I’d add a sweater or 2 – cotton for summer, but good with A/C. A 3/4 length sleeve perhaps.

I don’t think you need to go more feminine, but just a shirt + pants doesn’t look “finished” to me. I’d stick with those shapes, if you like them but try to add something extra every day- sweater, fun necklace, cute shoes, belt, etc. And make sure the rest of you is finished- no wet hair to work etc.

Invest in a good quality bag, maybe a satchel type that could also hold documents in a pinch.

The devil’s in the details–it’s adding a scarf, a piece of jewelry, It’s checking your outfit for proper fit, but it is also making sure all your buttons are on, loose threads are snipped, no stains–and for heaven’s sake, iron your clothes or have them professionally done. Be sure your nails are manicured–not necessarily polished, but clipped, clean. Shoes-polish them and check for heels that are “running down”-get them to the shoe repair shop, or discard altogether.

When you purchase something new, be sure it will mix/match well with what’s already in your closet–it gives you more variety when you put an outfit together. Most of my work wardrobe is composed of separates for this reason.

I agree with the feminine v. professional and Nordstrom shopper points above, but I wanted to highlight the ease of a well tailored suit for people who find it hard to match things on their own. The best way to look more professional is to wear a jacket that fits, whether it is over a dress or part of a suit. Get to know the lady in your dry cleaners who does tailoring. They are life savers.

I know from experience that it can be hard for us short curvy girls to find the right fit in professional wear. Big boobs mean you have to upsize button down shirts to get them to button without gapping but then the arms and shoulders are too big. My go to pieces on top are matching cardigans & tees or tanks in a variety of colors (brights & neutrals) and different necklines and sleeve lengths. On the bottom, look for a-line skirts in non-clingy materials that will flow off of your widest part. Same for pants as a boot cut or wide trouser leg will balance out hips better than a tapered leg. Always buy pants that fit your hips and then you can tailor the parts that don’t fit. I like to go neutralon the bottom and bring in color more on top. My staples are a pair of solid color pants in black, gray, olive, tan, and dark brown, and a pair of black with a thin pinstripe and one in a gray herringbone weave pattern. On the cheaper end try express or loft or gap to start building up basics and then work up to nicer stores for a few great items to mix in. To snazz things up a bit, look for cute necklaces and bracelets. A little sparkle even if it’s a $10 necklace from target finishes things off. I suggest you stay away from fake metal jewelry and go with beads or stones when buying cheaper jewelry. Good luck!

I went back over everyone’s comments, and I have tried to compile a list of things to look at. If anyone sees anything that I have left off or is a must or is listed but I should remove, please let me know. (Remember, I’m on the heavier side with a chest and bottom)

I think the size of everyone else’s wardrobe is not as important as something you feel is manageable. That said, I think having options that work in different settings is more important. A must is a full-on suit that can be broken up (no reason not to make it a pants suit). Since you did not mention that you have a suit, I assume that is not a daily requirement in the rest of my suggestions. Round off your top with a few tailored/structured cardigans and maybe another blazer. For layering, get a few silk tees and button-up blouses in silk. Keep the pants you have and maybe add two more pair, maybe one in a pattern. If you want to add a dress or a skirt, feel free, but that is not mandatory, even in Dallas. For “flair” try some silk scarves tied as a cravat or knotted like a loose tie and even interesting belts if your pants have belt loops. That can add color and interest without forcing you into the realm of jewelry, which can be complicated if its not your thing.

My personal opinion is that an executive, you should probably be able to go two weeks without completely repeating an “outfit.” That does not mean repeating pieces, just not the exact same combination. My executive goes about 6 weeks to two months without repeating (CFO for large non-profit). I’ve never tracked it, but she definitely rotates her clothing enough so its not noticeable that she is wearing the “Monday” blouse again. She has a very classic and simple style –using the pieces I have listed above. She has never worn a dress. She does have some skirt suits and a few more casual print skirts she matches with a shell and cardi. She wears the same diamond pendant every day, a watch, small earrings and maybe a bracelet. At Christmas, she has a few sterling silver pins she clips to her blazers.

I feel more comfortable in pants than in dresses and skirts so I’d say a basic starting wardrobe would have at least 5 pairs of pants. That way you have a week’s worth of bottoms without repeats. Although if they are basic and neutral colors, you could easily repeat pairs if needed and nobody would notice. Black pants are black pants. As you find skirts you like, add 2-3 of those, especially if they are more comfortable in the summer heat. They are easily mixed in if everything you have is complimentary color-wise. To make them last, I take off my work pants when I get home, spot clean if needed and then hang them up for a second wearing. I only dry clean or wash after one wearing if really wrinkled or stained. For tops, you probably would want at least 10 top options since they aren’t as easily rework and they are more noticeable on repeat wearing. You’ll need mostly tops that can be worn alone or as a bottom layer and then you can mix in 2-3 top layer options like a blazer or cardigan. Again, make sure everything can be mixed color-wise. For shoes, you could get by with a black pair and a brown pair but I suggest getting one more pair in a fun texture or color for variety. I like having a pair of burgundy red flats or heels since I often wear all black or black and gray. Nobody will notice if you repeat your shoes often as long as you keep them in good shape and buy new ones when needed. I hope that helps!

I would pay attention to how people talk about how you look. I tend to get a bit lax at work sometimes (I am always bouncing between courts and running around, so there is temptation to be comefortable), but I noticed that when I wear a dress or actually TRY and do my makeup or hair people in the office comment or ask if I have a date. This sparked me to wear more skirt suits or dresses. Dresses are the easiest, no thinking involved and you tend to look more sophisticated.

I’m not sure if anyone keeps up with previous articles, but I thought I would post an update.

I took your advice, went to Nordstrom and took advantage of their personal shopper. While I went in thinking I would spend $150 – $200 on a couple of pieces, in the end, I spent $800.00 on several pieces.

Normally, this would be a bad bad thing, but it was just the opposite. I had a great time and I love my clothes!

Normally, I hate shopping. I never find anything that looks good given my body structure and lack of color coordination and after a while I simply get tired, depressed and leave. With the personal shopper, everything was already picked out waiting for me in the dressing room. I found that I wear a 16 petite and I picked up some staples along with some cute clothes. ACTUALLY CUTE clothes!

I don’t know if I can afford shopping at Nordstrom often, but I know if I shop there in the future, I will always use their personal shopper.

As for the items, well, I purchased the following:

a black ankle length skirt
a couple of tops (purple, brown, turquoise)
a blue and green scarf
a brown cardigan
a couple of sweaters tops (I get cold easily and winter is coming)
a pair of dark brown pants
a pair of nude shoes
a set of earrings and a necklace

While I believe I still need some more tops given I usually repeat clothing every week, I am very happy with my start and I appreciate everyone’s helpful advice.